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Merck

803413

Sigma-Aldrich

SDA (NHS-Diazirine) (succinimidyl 4,4′-azipentanoate)

Sinónimos:

2,5-Dioxo-1-pyrrolidinyl 3-methyl-3H-diazirine-3-propanoate, NHS-diazirine Succinimidyl 4,4′-azipentanoate, SDA, Succinimidyl-diazirine

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About This Item

Fórmula empírica (notación de Hill):
C9H11N3O4
Peso molecular:
225.20
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.22

Análisis

≥90%

Nivel de calidad

formulario

powder

mol peso

225.2

idoneidad de la reacción

reagent type: cross-linking reagent

condiciones de almacenamiento

desiccated

solubilidad

DMSO or DMF: soluble

Condiciones de envío

ambient

temp. de almacenamiento

2-8°C

cadena SMILES

CC1(N=N1)CCC(ON2C(CCC2=O)=O)=O

InChI

1S/C9H11N3O4/c1-9(10-11-9)5-4-8(15)16-12-6(13)2-3-7(12)14/h2-5H2,1H3

Clave InChI

SYYLQNPWAPHRFV-UHFFFAOYSA-N

Descripción general

Succinimidyl-diazirine (SDA) reagents are a new class of crosslinkers that combine proven amine-reactive chemistry with an innovative and efficient diazirine-based photochemistry for conjugating amine-containing molecules to nearly any other functional group. The SDA crosslinkers include six compounds differing in spacer arm lengths, ability to cleave the crosslinked proteins, and presence or absence of a charged group for membrane permeability. Protein crosslinking is an important technique used to understand protein structure and to stabilize protein-protein interactions, and these SDA reagents extend the efficiency and range of interactions that can be explored by this approach.

Características y beneficios

  • Membrane-permeable—suitable for in vivo intracellular protein crosslinking
  • Heterobifunctional—NHS ester group reacts with primary amines at pH 7 to 9 to form covalent amide bonds; diazirine (azipentanoate) group reacts efficiently with any amino acid side chain or peptide backbone upon activation with long-wave UV light (330-370 nm)
  • Controllable—two-step chemical crosslinking is activated using common laboratory UV lamps
  • Easy to use—these crosslinkers are photo-stable under typical laboratory lighting conditions so there is no need to perform experiments in the dark
  • Better than aryl azides—the diazirine photoreactive group has better photostability in normal light than phenyl azide groups of traditional photoreactive crosslinkers, yet the diazirine group is more efficiently activated by long-wave UV light

Precaución

This product is sensitive to moisture. The vial is packaged in a resealable bag with a desiccant to reduce exposure to moisture. After cold storage, equilibrate the vial to room temperature before opening to reduce condensation inside the vial. Make fresh solutions. Storage of stock solutions is not recommended. After use, return the vial to the resealable bag. Close the bag and store the product at the recommended temperature.

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Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Photoactivatable crosslinking sugars for capturing glycoprotein interactions.
Yoshihito Tanaka et al.
Journal of the American Chemical Society, 130(11), 3278-3279 (2008-02-26)
Monika Suchanek et al.
Nature methods, 2(4), 261-267 (2005-03-23)
Protein-protein interactions are the key to organizing cellular processes in space and time. The only direct way to identify such interactions in their cellular environment is by photo-cross-linking. Here we present a new strategy for photo-cross-linking proteins in living cells.

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